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In the first proven SN2' fullerene reaction, both C3 and C1 C60F36 hydrolyse to C1 isomers of C60F35OH that eliminate HF to give epoxides C60F34O; C60F36O oxides are shown to be ethers, and a fourth isomer of C60F36 exists

In the first proven SN2' fullerene reaction, both C3 and C1 C60F36 hydrolyse to C1 isomers of C60F35OH that eliminate HF to give epoxides C60F34O; C60F36O oxides are shown to be ethers, and a fourth isomer of C60F36 exists
In the first proven SN2' fullerene reaction, both C3 and C1 C60F36 hydrolyse to C1 isomers of C60F35OH that eliminate HF to give epoxides C60F34O; C60F36O oxides are shown to be ethers, and a fourth isomer of C60F36 exists
On standing in organic solvents containing traces of water, C3 and C1 isomers of C60F36 slowly convert to C1 isomers of C60F35OH. Both fluorofullerenols eliminate HF during EI mass spectrometry to give C60F34O epoxides, one fullerenol being much less stable than the other to the extent that the mass spectrum shows only the epoxide. Both C60F35OH isomers have C1 symmetry, one being identified by the remarkable linear relationship between chemical shifts in its 19F NMR spectrum and those in the spectrum of C1 C60F36; the spectrum of the other shows the pattern of C3 C60F36 rendered asymmetrical by the replacement of one F by OH. The reactions are facilitated by the presence of isolated double bonds, and provide the first proven examples of an SN2' reaction of a fullerene derivative. Our observation explains why only a limited number of fluorines are readily replaced in C60F36 and why C60F18 is by contrast much more resistant to hydrolysis. We have isolated also a pure isomer of C60F36O, which is shown to be an oxahomofullerene (ether) apparently derived from C1 C60F36, and an impure fraction comprising a fourth isomer of C60F36, a trifluoromethyl derivative of C60F36, a second isomer of C60F36O, and an unknown species of 1392 u.
electrophilic aromatic-substitution, nucleophilic-substitution, fluorinated c-60, derivatives, fullerene, arylation, c60cl6
1477-0520
1026-1033
Avent, Anthony G.
6fe5d51d-5f31-454f-938a-ec91c840f2ce
Abdul-Sada, Ala'a K.
766a024d-ab64-4a35-8eff-99d86b13b987
Clare, Brian W.
eea67c37-7045-4eae-9600-4112dfd244fd
Kepert, David L.
afcaa306-d2e7-40cc-85ec-49b5981d1275
Street, Joan M.
186366c0-692b-4236-bb93-e2a3b6e9395c
Taylor, Roger
16cca243-6646-4c6f-a563-321c2b1bb0f6
Avent, Anthony G.
6fe5d51d-5f31-454f-938a-ec91c840f2ce
Abdul-Sada, Ala'a K.
766a024d-ab64-4a35-8eff-99d86b13b987
Clare, Brian W.
eea67c37-7045-4eae-9600-4112dfd244fd
Kepert, David L.
afcaa306-d2e7-40cc-85ec-49b5981d1275
Street, Joan M.
186366c0-692b-4236-bb93-e2a3b6e9395c
Taylor, Roger
16cca243-6646-4c6f-a563-321c2b1bb0f6

Avent, Anthony G., Abdul-Sada, Ala'a K., Clare, Brian W., Kepert, David L., Street, Joan M. and Taylor, Roger (2003) In the first proven SN2' fullerene reaction, both C3 and C1 C60F36 hydrolyse to C1 isomers of C60F35OH that eliminate HF to give epoxides C60F34O; C60F36O oxides are shown to be ethers, and a fourth isomer of C60F36 exists. Organic & Biomolecular Chemistry, 1 (6), 1026-1033. (doi:10.1039/b209760p).

Record type: Article

Abstract

On standing in organic solvents containing traces of water, C3 and C1 isomers of C60F36 slowly convert to C1 isomers of C60F35OH. Both fluorofullerenols eliminate HF during EI mass spectrometry to give C60F34O epoxides, one fullerenol being much less stable than the other to the extent that the mass spectrum shows only the epoxide. Both C60F35OH isomers have C1 symmetry, one being identified by the remarkable linear relationship between chemical shifts in its 19F NMR spectrum and those in the spectrum of C1 C60F36; the spectrum of the other shows the pattern of C3 C60F36 rendered asymmetrical by the replacement of one F by OH. The reactions are facilitated by the presence of isolated double bonds, and provide the first proven examples of an SN2' reaction of a fullerene derivative. Our observation explains why only a limited number of fluorines are readily replaced in C60F36 and why C60F18 is by contrast much more resistant to hydrolysis. We have isolated also a pure isomer of C60F36O, which is shown to be an oxahomofullerene (ether) apparently derived from C1 C60F36, and an impure fraction comprising a fourth isomer of C60F36, a trifluoromethyl derivative of C60F36, a second isomer of C60F36O, and an unknown species of 1392 u.

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More information

Published date: 2003
Keywords: electrophilic aromatic-substitution, nucleophilic-substitution, fluorinated c-60, derivatives, fullerene, arylation, c60cl6

Identifiers

Local EPrints ID: 19884
URI: http://eprints.soton.ac.uk/id/eprint/19884
ISSN: 1477-0520
PURE UUID: 4a332681-3d63-45e7-9bb3-e9beee37d009

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Date deposited: 23 Feb 2006
Last modified: 08 Jan 2022 18:50

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Contributors

Author: Anthony G. Avent
Author: Ala'a K. Abdul-Sada
Author: Brian W. Clare
Author: David L. Kepert
Author: Joan M. Street
Author: Roger Taylor

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